


Punish Me

by HisAngelThursday



Category: Supernatural
Genre: Corporal Punishment, Dean in Panties, Dom Castiel, Forced Crossdressing, Forced Feminization, Humiliation, M/M, Non-Consensual Spanking, Paddling, Public Humiliation, Spanking, Student Dean, Sub Dean, Teacher Castiel
Language: English
Status: Completed
Published: 2017-07-10
Updated: 2017-07-10
Packaged: 2018-11-30 11:10:59
Rating: Mature
Warnings: Rape/Non-Con, Underage
Chapters: 1
Words: 3,031
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11462367
Author URL: https://archiveofourown.org/users/HisAngelThursday/pseuds/HisAngelThursday
Summary: After being framed for something he didn't do by a jilted cheerleader, Dean finds himself being punished by the school's sexiest teacher.





	Punish Me

**Author's Note:**

> A conglomeration of some of my favorite fictional kinks. "Fictional" being the key word here, obviously -- little to none of this stuff would be at all healthy in a real-life setting, and shouldn't be treated as such. 
> 
> Dean's about sixteen or seventeen here, and I tagged it "non-con" only because some aspects (the crossdressing, the spanking) aren't consensual. Both parties are into everything else though, so technically there isn't any rape. 
> 
> In any case, I might continue this if y'all are interested, so let me know!

Dean never thought he'd find himself saying it, but he was losing interest in girls. Guys too, for that matter. There was absolutely only one person in the world who Dean could seem to think about now, and that was Castiel Novak.

His history teacher.

The guy was young, as teachers went, only in his mid to late twenties. Constant sex hair and chapped lips and piercing blue eyes that seemed to look directly into his soul. And his _voice._ Now, _that_ was the kind of voice Dean would pay big money to hear bossing him around.

He was the number one subject of Dean's sexual fantasies, the star of every one of his wet dreams, and the only person he was currently interested in dating.

There was only one foreseeable issue with this, and that was that Dean had already established himself as the town tart. Everyone expected to get some with him, and it made things a little awkward when he just wasn't in the mood.

Like now, for example.

“What do you mean you don't want to go out with me?” Lisa Braden squawked. “I am the _head cheerleader!_ Do you have any idea how many guys would _kill_ to get in my pants!?”

“Sorry sweetheart,” Dean shrugged, leaning casually against the hood of his Impala. “I don't know what else to tell you. What can I say? I got eyes for another.”

Lisa's posse of homogeneous fellow cheerleaders giggled behind her, till Lisa wheeled on them with a glare. They fell silent instantly, looking dutifully at their shoes.

She turned back to him, eyes narrowed and disdainful. “You will pay for this, Dean Winchester. Your days of being top dog at this school are _over._ ”

She turned on her heal and marched away, her personal trio of harpies following along behind her.

“No means no, sweetheart!” Dean called after her.

He sighed. It wasn't that he disliked Lisa – wasn't like she wasn't smart, she got some of the best grades in the entire school. And she did a lot of volunteer work, so it wasn't like she was 100% shallow. She just needed to get over herself a little and grow out of her extended Mean Girls phase.

Dean sighed, hopping off the hood of his Impala and dusting off his lucky leather jacket, all set to be fashionably late for yet another history class. With Mr. Novak.

Now _that_ was something Dean was looking forward to – he made a mental note to suck on his pencil, do that special bedroom grin he'd been practicing that couldn't help but make the recipient think of sex. Of course, Novak had shown no indication of being affected in any way by Dean's flirtations, eyes as steely and impassive as ever, but Dean wasn't the sort of person to give up easily unless actively discouraged.

He walked towards the school, set to be fashionably late as ever.

Utterly unprepared for what was going to happen to him inside.

 

…

 

All heads turned towards Dean as he walked into the door. This, in and of itself, was nothing new, but there was something about the knowing smiles and giggles that permeated the room that made Dean think he'd missed something important.

That's when he looked towards the desk, Novaks expression even flintier (re: hotter) than it usually was. Beside him stood an indignant looking Lisa Braden and her dutifully indignant posse.

“I'm sorry, did I miss a notification telling me I was today's sub?” Dean huffed, trying to cover how nervous the whole situation was making him. “'Cause I gotta let y'all know ahead of time, I don't know shit about teaching history.”

A muffled giggle regurgitated through the class.

“Adorable, Mr. Winchester,” Novak deadpanned. “I suppose you have absolutely no idea what you did today, correct?”

“Sure I do: I woke up at seven, I made some toast-”

  
“ _Dean_ ,” Novak cut him off sharply. Dean shivered at the use of his name. “I know you think you're hilarious, but do you mean to tell me you know nothing about lifting Miss Braden's skirt without her consent?”

Dean blanched, eyes widening. “I did _not!_ ”

“Oh, really? Well, I have three witnesses present saying you did.” Novak gestured to the three harpies behind her.

“They're lying!” Dean sputtered.

“Oh, I'm _sure_.”

“No, look – Lisa here, she's been trying to get me to go out with her, right? So she comes up to me today, and she's like -”

“Dean,” Novak snapped. “Contrary to the image you so carefully attempt to convey of delinquency, you are a bright young man. I've seen your grades, your grasp of information, and I'm well-aware that you're not as dim-witted as you, for whatever reason, want people to think.”

“...Thanks?”

“That said, you are anything but a model student,” Novak continued. “You completely disregard student dress code, you routinely disrupt class, you're rude, disrespectful, have open contempt for authority, and are incessantly and inappropriately lewd and flirtatious. And now you'd like me to believe that you'd pass up the opportunity to look at the head cheerleader's underwear?”

“Hey, I respect consent, okay? Unlike some folks around here,” Dean added, with a glower at a now smug Lisa.

“I'm sure. In any case, Miss Braden, you may take your seat; rest assured, Mr. Winchester's punishment will be doled appropriately.”

Lisa smiled smugly, tossing her hair as she practically flounced back over to her chair with her subordinates. The room was practically tittering with excitement; they knew how infamously harsh the punishments at this school could be.

  
Dean gaped. “That's not fucking fair!”

“Language, Mr. Winchester,” said Novak lightly, rummaging in his desk drawer. “You've had this coming for a long time.”

Dean could only watch, with both fear and morbid curiosity, as Novak retrieved a bundle of clothes and held them out to him.

“Since your so fond of ignoring the school dress code,” said Novak coolly. “Perhaps you need a reminder of what a school uniform looks like, correct?”

Dean looked at the uniform, brow furrowed in confusion. “Mr. Novak, this is, uh...”

“A girl's uniform? I know.”

Several gasps and giggles permeated the room. Dean's face drained of color.

“Since you seem to like objectifying women so much, I thought you might like to dress like one.” Novak pointed to the supply closet. “Change in there, please. I'd direct you to the men's room, but then, that would be counterproductive wouldn't it?”

The class tittered like delighted squirrels. Dean wanted to smack each and every one of them.

“Mr. Novak, I can't -”

“ _Now, Dean._ I assure you, you do not want the principal involved in this. Or your father,” he added.

Dean shuddered. As bad as the punishments at school could be, the heavy end of the belt was worse.

He looked down at the bundle of clothes in Novak's hand, a flush of shame slowly spreading across the bridge of his nose. He'd always been a bit insecure about his appearance, always thought he was a little too effeminate for the image of masculinity he was trying to convey. A punishment like this couldn't have been more hand tailored to his insecurities if he'd selected it himself.

But there was nothing he could do. The last thing he wanted was his father getting involved in this.

Quietly, he accepted them and made his way to the supply closet.

…

 

Dean felt numb as he slid the skirt over his smooth legs. He'd rather the entire class – and probably the entire school, at the rate these people talk – to know that he liked to keep himself shaved, but then, life didn't seem to care what his preferences were, did it?

He shuddered as he slid the waistband over the pink lace of his panties. Novak hadn't given him any underwear to wear with the ensemble, and he didn't have any others to change into. Obviously, the odds of anyone actually seeing them and knowing they were his were minimal, but the skirt – which, he noted, was a couple sizes too small for him – made him feel awfully exposed and vulnerable.

He buttoned up the white blouse, hoping his nipples wouldn't show through without a bra. Normally, anything that might arouse Novak would be a plus, but today everything seemed to only exacerbate his humiliation.

“Don't dawdle, Mr. Winchester,” Novak chided, from outside the door. “I do have a class to run.”

Dean squeezed his eyes shut, vowing to get this humiliation over with as soon as possible. “Yes, Mr. Novak.”

He pulled up the white knee socks, and pulled his boots on over them, lacing them up as quickly as possible.

He steadied himself, and let his hand linger on the cold doorknob – questioning, hopelessly, futilely, if there was any way out of this – before swallowing hard and stepping out to face the music.

The class didn't even attempt to contain its delight at the situation, and Dean felt his face growing redder by the second. He didn't dare take his eyes off the floor.

“May I please take my seat now, Mr. Novak,” he said, voice uncharacteristically quiet.

“Not quite yet, Dean. Look at me, please.”

It took considerable effort to overcome his shame long enough to drag his eyes off the floor. They widened considerably when he saw that in his hands, he held a paddle.

“Mr. Novak, you can't be -”

“I am, Dean. The school takes this offense extremely seriously. Now, bend over the desk.”

“Please, Mr. Novak, I'll do -”

“ _Now_ , Dean.”

Dean swallowed hard, feeling ready to cry. He chanced a glimpse out over the class, hoping for a little sympathy, but all he saw were faces grinning with impish glee at his situation. Lisa looked as though she was preening in her own victory.

His ears burned hot as he complied, once again lowering his gaze and reluctantly putting his hands on Mr. Novak's desk. He flushed all the way from his neck down to his shoulders as he felt Novak's hand drawing the ridiculously short skirt up over his buttocks.

Several of his classmates audibly gasped, and Mr. Novak chuckled, low and dark and predatory. “Mr. Winchester, I don't recall giving you any panties to wear with your uniform.”

The class practically exploded with laughter. Dean's face felt like it was on fire. “I-I can explain -”

“Quiet, Mr. Winchester. I do not recall giving you permission to speak.”

Dean swallowed hard. Nothing about this situation was good, but goddamned if that voice wasn't going straight to his cock. He glared at it warningly – the last thing he needed right now was a hard on to make his humiliation complete.

“Now, given your already substantial punishment, I will spare you having to count,” Mr. Novak said coolly. “But I will by giving you twenty strokes with the paddle, ten on each cheek. If you at any point take your hands off the desk, I will give you ten more. Do you understand?”

Dean nodded, eager to get this over with. He yelped as Novak's bare palm smacked him across one cheek. “Answer me, Dean.”

“Yes, sir!” Dean cried out, not even questioning where his use of 'sir' came from.

Novak chuckled darkly. “Good boy,” he purred, and Dean's cock gave a throb. “I am going to begin now.”

The spanking went quicker than Dean expected, but somehow that didn't improve matters. He felt the way his cheeks jiggled slightly with each stroke, the prickling, tender flesh rapidly growing pink. The way his classmates snickered with each and every clap of the paddle. He knew he'd be remembering this for a long, long time.

And the worst part was, part of Dean loved it.

He tried not to think about that too much. He just kept his head low to the desk and focused on keeping his eyes from welling over and not getting hard.

Finally, Novak set the paddle down beside him, and pulled the skirt down over his glowing buttocks.

“Very well, Mr. Winchester. You may take your seat.”

In that moment, part of Dean wanted to slap the guy. How could he be so calm after humiliating Dean this way?

Nevertheless, Dean quietly complied, thankful that the skirt obscured his semi. He couldn't meet any of his snickering classmates' eyes as he took his seat, keeping his own trained on the desk. He winced at the unforgiving wooden chair beneath his tender ass.

Lisa looked smugly over her shoulder at him. “Bet you wish you hadn't turned me down now, hmmm?”

Dean, of course, said nothing.

“Alright then,” Novak announced, at the front of the room. “Today, we will be resuming our discussion of the Romans.”

…

 

Castiel barely suppressed a smirk as his students filed out of the classroom, Dean dutifully remaining in his seat to collect his confiscated clothing.

Predictably, not a lot of actual learning had gotten done that period, everyone a little too preoccupied with Dean's predicament to focus much on the lesson itself, but that was alright. It was good for moral. And Castiel had been waiting for the excuse to do something like that for a long, long time.

Dean had seemed so deliciously ashamed of himself when he'd been handed the girls' clothing, and even more so after he'd put them on, that Castiel had almost felt bad for him. Almost.

The little punk had been giving him hard-ons since the start of the semester, all cocky smirks and swagger and oh-so-skillfully drawing Castiel's attention to those plush, perfect lips with the pens he liked to suck on. It was an oral fixation, for crying out lout. It shouldn't have been so sexy.

Once, he'd brought a bottle of coca cola to class, and had spent the entire period subtly miming fellatio. Castiel had nearly jizzed in his pants by the time the bell rang, and had to jack off in the staff bathroom before he could resume his daily routine.

  
He'd known right then that he was going to put Dean Winchester in his place if it was the last thing he did.

This was part of the real reason why Cas couldn't help but feel smug with how uncharacteristically meek Dean had been throughout the entire class period, blushing face trained on his workbook and, for once, never causing any actual disruptions. It was just as it should have been.

Now, there was just one thing that could make this afternoon perfect.

He looked up from his notes to see Dean standing over him, cheeks and ears still red and freckles darkened.

Castiel smiled, playing dumb. “Something I can help you with, Dean?” he inquired.

He expected Dean to ask for his pants back, maybe cuss him out for putting him through such a thing.

Dean wet his lips, eyes downcast. “I didn't look under Lisa Braden's skirt,” he muttered. “I wouldn't do shit like that.”

“Oh?” said Castiel, hands folding neatly in front of him. “And why would she lie about such a thing, hmmm?”

“She asked me to go on a date with her,” Dean answered quietly. “I said no. Think it hurt her ego.”

Castiel smiled softly. “And why would you say no, Dean? She's a very attractive girl. The head cheerleader, in fact.”

Dean rolled his eyes. “I know that.” Frustration was evident in his voice. “Jesus, everyone keeps fuckin' saying that like it makes her the end-all and be-all of human existence or some shit.”

“Language, Dean,” Castiel chastised, and Dean's eyes lowered. Cas decided he liked this submissive side of him. “And you did not answer my question: why did you turn down Lisa Braden, Dean?”

Dean blinked, opened his mouth, and closed it again. He closed his eyes and blushed harder. “'Cause, I...I kinda got the hots for someone else, okay?”

Castiel smiled darkly, leaning back in his chair. “Oh? And who would that be, Dean?”

Dean swallowed hard, wetting his lips. “That's, uh...s'kinda my business, isn't it?”

“Oh, I don't know,” Castiel drawled. “The way you've been shamelessly tormenting me, making my cock harder than any partner's made it in years...it would seem to me that sort of makes it my business, wouldn't you agree?”

Dean's eyes flew open, wide and confused and _green_. “H-huh?”

Castiel chuckled. “Dean,” he said, finally ready to let the cat out of the bag. “I know you didn't look under Lisa Braden's skirt.”

Dean couldn't seem to bring himself to say anything, staring at him in sheer bafflement. Cas smiled, beckoning for Dean to join him behind the desk, and Dean slowly, tentatively complied.

Cas was once again stunned by how sexy he looked in that getup, cheeky little nipples hard and pink beneath the thin white fabric and skirt too short for his smooth, meaty thighs. The knowledge that underneath that skirt was a freshly spanked ass and lacy pink panties – that Dean had worn on his own volition, mind you – was enough to make Castiel painfully hard.

With rough hands he tugged Dean onto his lap, causing the boy to give an undignified squeak. Castiel guided his chin towards the classroom window.

Outside of it was Dean's Impala, clearly visible.

“ _That_ ,” Cas told him. “Is where I saw your altercation with Miss Braden. I know for a fact you didn't instigate it, and at no point did you look under her skirt.”

Dean turned to look at him, brow furrowed. “So why did you punish me?”

Castiel stared at him. Everything about him in that moment seemed so completely perfect: the delicate fans of his eyelashes, the faint flush lingering in his cheeks, the smattering of freckles. The way he so delectably said the words “punish me.”

Wordlessly, Castiel knotted his fingers in the short caramel strands of his hair and guided those plush, half-open lips to his own.

Dean felt so relaxed against him, so perfectly submissive as he leaned into the kiss, not even questioning what Castiel was doing. He felt as though he could have come right then and there.

Castiel pulled away, looking down at the boy with darkened eyes. “Go lock the door, Dean,” he growled. “I'll show you why.”

 


End file.
